ChemicalBook CAS DataBase List O-Desmethylvenlafaxine

O-Desmethylvenlafaxine synthesis

11synthesis methods

Product Name:O-Desmethylvenlafaxine
CAS Number:93413-62-8
Molecular formula:C16H25NO2
Molecular Weight:263.38

Desvenlafaxine is chemically derived from 4-benzyloxyphenylacetic acid, by first converting to the acid chloride with oxalyl chloride and then condensing with dimethylamine to produce the corresponding N,N-dimethyl amide. Deprotonation of the amide with butyllithium, followed by condensation with cyclohexanone gives a b-hydroxyamide intermediate, which is reduced with alane, and debenzylated by using palladium on carbon and 1,4-cyclohexadiene to produce desvenlafaxine.

93413-69-5 Synthesis

93413-69-5
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$10.00/1mg

93413-62-8
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$5.00/5mg

Yield:93413-62-8 98%

Reaction Conditions:

with potassium hydroxide in ethylene glycol at 195 - 200; for 24 h;Inert atmosphere;

Steps:

1 Example 1:
To a clean flask , 250g of 1- [2 -(Dimethyl amino- l-(4-methoxyphenyl) ethyl cyclohexanol, lit of ethylene glycol, 100 g of polyethylene glycol-400 and 350 g of Potassium hydroxide are added, under nitrogen atmosphere. Reaction mixture is then heated under nitrogen, by raising the temperature to about 195-200 °C over a period of about 3-4 h. The same temperature is then, continuously maintained for a period of 24 h. The temperature of the reaction mixture is loweredto a temperature of about 50°C and diluted with water and extracted with lit of toluene. Toluene is concentrated in order to obtain unreacted l-[2-(Dimethyl amino- l-(4-methoxyphenyl) ethyl cyclohexanolof about 95g to about TOOg. Water layer is then acidified to pH 4 to getl-[2- (Dimethylamino)-l-(4-hydroxyphenyl)ethyl]-cyclohexanol.On drying the mixture at a temperature ranging from about 75 °C to about 80°C for 8 hours, l-[2-(Dimethylamino)-l-(4- hydroxyphenyl)ethyl]-cyclohexanol, is obtained (125-130g) with a purity of 99.25% measured by HPLC). Yield percentage based on recovery of unreacted l-[2-(Dimethyl amino-l-(4- methoxyphenyl) ethyl cyclohexanol is 98%.

References:

R L FINECHEM PRIVATE LIMITED;A RAMAKRISHNA, Ramesha;S MARAVANAHALLI, Siddegowda;MAHIL, Santosh WO2018/146529, 2018, A1 Location in patent:Page/Page column 10

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